19837-81-1

Basic information

• Product Name: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE
• Synonyms: benzenesulfonamide, 4-amino-N-(3-chlorophenyl)-
• CAS NO: 19837-81-1
• Molecular Formula: C₁₂H₁₁ClN₂O₂S
• Molecular Weight: 282.75
• Mol File: 19837-81-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 467 °C at 760 mmHg
• Flash Point: 236.3 °C
• Appearance: /
• Density: 1.466 g/cm³
• Vapor Pressure: 6.73E-09mmHg at 25°C
• Refractive Index: 1.674
• CAS DataBase Reference: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-81-1)
• EPA Substance Registry System: 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE(19837-81-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 19837-81-1(Hazardous Substances Data)

Usage

General Description

4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is a chemical compound with the molecular formula C12H11ClN2O2S. It is a sulfonamide derivative with an amino group and a chlorophenyl group attached to the benzene ring. 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is commonly used as a pharmaceutical ingredient in the production of drugs with antibacterial and diuretic properties. It works by inhibiting the growth of bacteria and promoting the excretion of excess water and salts from the body. 4-AMINO-N-(3-CHLORO-PHENYL)-BENZENESULFONAMIDE is an important component in the synthesis of medications used to treat urinary tract infections, high blood pressure, and other related conditions.

InChI:InChI=1/C12H11ClN2O2S/c13-9-2-1-3-11(8-9)15-18(16,17)12-6-4-10(14)5-7-12/h1-8,15H,14H2

Upstream product

• 103-84-4 Acetanilid 
• 108-42-9 3-chloro-aniline 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 16937-05-6 3'-chloro-4-nitrobenzenesulfonanilide 
• 19837-98-0 N-acetyl-sulfanilic acid-(3-chloro-anilide) 

Downstream Products

• 1258977-91-1 6-hydroxy-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(3-chlorophenylsulfamoyl)phenyl]amide 
• 1258977-79-5 6-chloro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro[1,7]phenanthroline-3-carboxylic acid [4-(3-chlorophenylsulfamoyl)phenyl]amide 
• 1262334-06-4 2-[(2,6-dichlorophenyl)amino]-N₁-(3-chlorophenyl)-N₄-phenylacetoxyacetamidobenzenesulfonamide 
• 444723-03-9 NU 6132 
• 114854-12-5 1,3-dihydro-5-1-(m-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-(p-tolyl)-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 114853-98-4 1,3-dihydro-5-1-(m-chlorophenyl)-p-sulphamylbenzeneazo>-1-(2'-naphthyl)-3-phenyl-2-thioxo-2H,5H-pyrimidine-4,6-dione 
• 116691-34-0 N-(3-Chloro-phenyl)-4-(8-hydroxy-quinolin-5-ylazo)-benzenesulfonamide 

Relevant articles and documents

Design, synthesis and biological evaluation of novel naphthoquinone-4-aminobenzensulfonamide/carboxamide derivatives as proteasome inhibitors

A series of novel 4-aminobenzensulfonamide/carboxamide derivatives bearing naphthoquinone pharmacophore were designed, sythesized and evaluated for their proteasome inhibitory and antiproliferative activities against human breast cancer cell line (MCF-7). The structures of the synthesized compounds were confirmed by spectral and elemental analyses. The proteasome inhibitory activity studies were carried out using cell-based assay. The antiproteasomal activity results revealed that most of the compounds exhibited inhibitory activity with different percentages against the caspase-like (C-L, β1 subunit), trypsin-like (T-L, β2 subunit) and chymotrypsin-like (ChT-L, β5 subunit) activities of proteasome. Among the tested compounds, compound 14 bearing 5-chloro-2-pyridyl ring on the nitrogen atom of sulfonamide group is the most active compound in the series and displayed higher inhibition with IC50 values of 9.90 ± 0.61, 44.83 ± 4.23 and 22.27 ± 0.15 μM against ChT-L, C-L and T-L activities of proteasome compared to the lead compound PI-083 (IC50 = 12.47 ± 0.21, 53.12 ± 2.56 and 26.37 ± 0.5 μM), respectively. The antiproliferative activity was also determined by MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) assay in vitro. According to the antiproliferative activity results, all of the compounds exhibited cell growth inhibitory activity in a range of IC50 = 1.72 ± 0.14–20.8 ± 0.5 μM and compounds 13 and 28 were found to be the most active compounds with IC50 values of 1.79 ± 0.21 and 1.72 ± 0.14 μM, respectively. Furthermore, molecular modeling studies were carried out for the compounds 13, 14 and 28 to investigate the ligand-enzyme binding interactions.

Synthesis, structural, biological and in silico studies of new 5-arylidene-4-thiazolidinone derivatives as possible anticancer, antimicrobial and antitubercular agents

A new series of halogenated 4-thiazolidinone derivatives bearing the sulfonamide moiety was synthesized and characterized via FT-IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray analysis. The newly synthesized target compounds were screened for their in vitro cytotoxicity on the HepG2 and MDA-MB-231 cell lines, and antimicrobial and antitubercular activity. The compounds showed promising anticancer activity towards the MDA-MB-231 cell line, and the trichloro derivatives with p-chloro substitution (6i) and p-hydroxy substitution (7e) exhibited excellent anticancer activity. Compounds 6b and 7c were observed to be moderate antimicrobial agents. The seven most potent anticancer agents were further studied for their antitubercular activity against an M. tuberculosis strain and it was found that compound 7e showed significant antitubercular activity. The potent candidates were also tested for hemolysis activity against human RBC cells and were found to be non-toxic. The mode of action for the observed anticancer activity was further supported by molecular docking studies of the potent compounds against the enzyme Aurora kinase (PDB ID: 4ZTR). Molecular dynamics (MD) simulations were further performed to study the stability of the ligand-protein complex.